N-Methyl-4-nitroaniline → N-Methyl-N-(4-nitrophenyl)cyclopropanecarboxamide

HRID 2381705Notes

Reaction equation

HRID 2381705 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.CCN(CC)CC.[CH:19]1([C:22](Cl)=[O:23])[CH2:21][CH2:20]1>C(Cl)Cl.CCOC(C)=O>[CH3:1][N:2]([C:3]1[CH:4]=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1)[C:22]([CH:19]1[CH2:21][CH2:20]1)=[O:23]

Participants

6

Reactant 3

HCID 7483N-Methyl-4-nitroanilineHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chloride

Product 1

HCID 66878005N-Methyl-N-(4-nitrophenyl)cyclopropanecarboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of N-methyl-4-nitroaniline (2 g, 13.1 mmol) in DCM (30 mL) was added Et3N (2.75 mL, 20 mmol) and cyclopropanecarbonyl chloride (1.32 mL, 14.4 mmol) at room temperature, after stirring for 1 h at room temperature, the mixture was diluted with EtOAc, the organics was washed with Sat. NaHCO3, brine, dried and concentrated to give N-methyl-N-(4-nitrophenyl)cyclopropanecarboxamide as crude product (3 g).

Workup

  1. washthe organics was washed with Sat. NaHCO3, brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3568edb35d86457bb56ffa6594809549
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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